(3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate

Three steps

• 4-fumarylacetoacetateReach from here →
  1. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)
  2. a quinone + succinate = fumarate + a quinol
  3. 4-fumarylacetoacetate + H2O = acetoacetate + fumarate + H(+)

  Catalysed by PRODH2, SDHB, FAH

• L-glutamineReach from here →
  1. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)
  2. trans-4-hydroxy-L-proline(out) + L-alanine(in) + Na(+)(out) = trans-4-hydroxy-L-proline(in) + L-alanine(out) + Na(+)(in)
  3. transport of alanine and glutamine (cytosol to extracellular)

  Catalysed by PRODH2, SLC1A4, SLC3A2, SLC7A5 and 1 moreinner side of the membrane, outer side of the membrane, extracellular space, cytosolOne of 10 routes

• CHEBI:18095Reach from here →
  1. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)
  2. trans-4-hydroxy-L-proline(out) + L-alanine(in) + Na(+)(out) = trans-4-hydroxy-L-proline(in) + L-alanine(out) + Na(+)(in)
  3. Transport of Hydroxy-Proline

  Catalysed by PRODH2, SLC1A4inner side of the membrane, outer side of the membrane, extracellular space, cytosol

• 2-aminoisobutanoateReach from here →
  1. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)
  2. trans-4-hydroxy-L-proline(out) + L-alanine(in) + Na(+)(out) = trans-4-hydroxy-L-proline(in) + L-alanine(out) + Na(+)(in)
  3. 2-aminoisobutanoate(out) + L-alanine(in) = 2-aminoisobutanoate(in) + L-alanine(out)

  Catalysed by PRODH2, SLC1A4, SLC7A10inner side of the membrane, outer side of the membraneOne of 2 routes

• N(omega),N('omega)-dimethyl-L-arginineReach from here →
  1. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)
  2. trans-4-hydroxy-L-proline(out) + L-alanine(in) + Na(+)(out) = trans-4-hydroxy-L-proline(in) + L-alanine(out) + Na(+)(in)
  3. N(omega),N('omega)-dimethyl-L-arginine + pyruvate = 5-(3,3'-dimethylguanidino)-2-oxopentanoate + L-alanine

  Catalysed by PRODH2, SLC1A4, AGXT2inner side of the membrane, outer side of the membrane

• pyridoxine 5'-phosphateReach from here →
  1. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)
  2. trans-4-hydroxy-L-proline(out) + L-alanine(in) + Na(+)(out) = trans-4-hydroxy-L-proline(in) + L-alanine(out) + Na(+)(in)
  3. L-selenocysteine selenide-lyase (L-alanine-forming)

  Catalysed by PRODH2, SLC1A4, SCLYinner side of the membrane, outer side of the membrane, cytosol

• a carboxylateReach from here →
  1. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)
  2. (S)-dihydroorotate + a quinone = orotate + a quinol
  3. orotate(out) + a carboxylate(in) = orotate(in) + a carboxylate(out)

  Catalysed by PRODH2, DHODH, SLC22A13inner side of the membrane, outer side of the membraneOne of 2 routes

• chlorine(.)Reach from here →
  1. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)
  2. trans-4-hydroxy-L-proline(out) + L-alanine(in) + Na(+)(out) = trans-4-hydroxy-L-proline(in) + L-alanine(out) + Na(+)(in)
  3. transport of alanine and chloride (cytosol to extracellular)

  Catalysed by PRODH2, SLC1A4, SLC6A14inner side of the membrane, outer side of the membrane, extracellular space, cytosolOne of 2 routes

• L-aspartateReach from here →
  1. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)
  2. trans-4-hydroxy-L-proline(out) + L-alanine(in) + Na(+)(out) = trans-4-hydroxy-L-proline(in) + L-alanine(out) + Na(+)(in)
  3. oxaloacetate + L-alanine = L-aspartate + pyruvate

  Catalysed by PRODH2, SLC1A4, AGXT2inner side of the membrane, outer side of the membrane

• (S)-dihydroorotateReach from here →
  1. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)
  2. a quinol + 2 Fe(III)-[cytochrome c](out) = a quinone + 2 Fe(II)-[cytochrome c](out) + 2 H(+)(out)
  3. (S)-dihydroorotate + a quinone = orotate + a quinol

  Catalysed by PRODH2, CYC1, UQCRFS1, DHODHouter side of the membraneOne of 2 routes

• nicotinateReach from here →
  1. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)
  2. (S)-dihydroorotate + a quinone = orotate + a quinol
  3. orotate(out) + nicotinate(in) = orotate(in) + nicotinate(out)

  Catalysed by PRODH2, DHODH, SLC22A12inner side of the membrane, outer side of the membraneOne of 2 routes

• beta-D-fructose 1,6-bisphosphateReach from here →
  1. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)
  2. a quinone + sn-glycerol 3-phosphate = dihydroxyacetone phosphate + a quinol
  3. beta-D-fructose 1,6-bisphosphate = D-glyceraldehyde 3-phosphate + dihydroxyacetone phosphate

  Catalysed by PRODH2, GPD2, ALDOA, ALDOB and 1 more

• thiosulfateReach from here →
  1. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)
  2. a quinone + succinate = fumarate + a quinol
  3. transport of fumarate and thiosulfate (cytosol to mitochondria)

  Catalysed by PRODH2, SDHB, SLC25A10mitochondrial matrix, cytosolOne of 3 routes

• D-cysteineReach from here →
  1. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)
  2. trans-4-hydroxy-L-proline(out) + L-alanine(in) + Na(+)(out) = trans-4-hydroxy-L-proline(in) + L-alanine(out) + Na(+)(in)
  3. D-cysteine(out) + L-alanine(in) = D-cysteine(in) + L-alanine(out)

  Catalysed by PRODH2, SLC1A4, SLC7A10inner side of the membrane, outer side of the membraneOne of 2 routes

• D-serineReach from here →
  1. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)
  2. trans-4-hydroxy-L-proline(out) + L-alanine(in) + Na(+)(out) = trans-4-hydroxy-L-proline(in) + L-alanine(out) + Na(+)(in)
  3. D-serine(out) + L-alanine(in) = D-serine(in) + L-alanine(out)

  Catalysed by PRODH2, SLC1A4, SLC7A10inner side of the membrane, outer side of the membraneOne of 6 routes

• D-ribose 1-phosphateReach from here →
  1. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)
  2. 1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamide + a quinone + H(+) = beta-nicotinamide D-riboside + a quinol
  3. purine nucleoside phosphorylase (nicotinamide)

  Catalysed by PRODH2, NQO2, PNPcytosol

• L-ornithineReach from here →
  1. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)
  2. trans-4-hydroxy-L-proline(out) + L-alanine(in) + Na(+)(out) = trans-4-hydroxy-L-proline(in) + L-alanine(out) + Na(+)(in)
  3. transport of alanine and ornithine (cytosol to extracellular)

  Catalysed by PRODH2, SLC1A4, SLC7A6inner side of the membrane, outer side of the membrane, extracellular space, cytosolOne of 3 routes

• gamma-Glu-AlaReach from here →
  1. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)
  2. trans-4-hydroxy-L-proline(out) + L-alanine(in) + Na(+)(out) = trans-4-hydroxy-L-proline(in) + L-alanine(out) + Na(+)(in)
  3. gamma-glutamyltransferase (alanine)

  Catalysed by PRODH2, SLC1A4, GGT1, GGT5 and 4 moreinner side of the membrane, outer side of the membrane, extracellular space, cytosol

• 1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamideReach from here →
  1. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)
  2. a quinol + 2 Fe(III)-[cytochrome c](out) = a quinone + 2 Fe(II)-[cytochrome c](out) + 2 H(+)(out)
  3. 1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamide + a quinone + H(+) = beta-nicotinamide D-riboside + a quinol

  Catalysed by PRODH2, CYC1, UQCRFS1, NQO2outer side of the membraneOne of 2 routes

• glycineReach from here →
  1. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)
  2. trans-4-hydroxy-L-proline(out) + L-alanine(in) + Na(+)(out) = trans-4-hydroxy-L-proline(in) + L-alanine(out) + Na(+)(in)
  3. L-Alanine:glyoxylate aminotransferase

  Catalysed by PRODH2, SLC1A4, AGXT, AGXT2inner side of the membrane, outer side of the membrane, mitochondrial matrixOne of 10 routes

• D-alanineReach from here →
  1. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)
  2. trans-4-hydroxy-L-proline(out) + L-alanine(in) + Na(+)(out) = trans-4-hydroxy-L-proline(in) + L-alanine(out) + Na(+)(in)
  3. D-alanine(out) + L-alanine(in) = D-alanine(in) + L-alanine(out)

  Catalysed by PRODH2, SLC1A4, SLC7A10inner side of the membrane, outer side of the membraneOne of 2 routes

• 2-(N(omega)-L-arginino)succinateReach from here →
  1. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)
  2. a quinone + succinate = fumarate + a quinol
  3. 2-(Nomega-L-arginino)succinate arginine-lyase (fumarate-forming)

  Catalysed by PRODH2, SDHB, ASLcytosolOne of 2 routes

• a 1-acylglycerone 3-phosphateReach from here →
  1. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)
  2. a quinone + sn-glycerol 3-phosphate = dihydroxyacetone phosphate + a quinol
  3. dihydroxyacetone phosphate + an acyl-CoA = a 1-acylglycerone 3-phosphate + CoA

  Catalysed by PRODH2, GPD2, GNPAT

• orotidine 5'-phosphateReach from here →
  1. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)
  2. (S)-dihydroorotate + a quinone = orotate + a quinol
  3. orotidine 5'-phosphate + diphosphate = orotate + 5-phospho-alpha-D-ribose 1-diphosphate

  Catalysed by PRODH2, DHODH, UMPS

• N(6)-(1,2-dicarboxyethyl)-AMPReach from here →
  1. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)
  2. a quinone + succinate = fumarate + a quinol
  3. N6-(1,2-dicarboxyethyl)AMP AMP-lyase (fumarate-forming)

  Catalysed by PRODH2, SDHB, ADSL, TNRC6BcytosolOne of 2 routes

• D-threonineReach from here →
  1. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)
  2. trans-4-hydroxy-L-proline(out) + L-alanine(in) + Na(+)(out) = trans-4-hydroxy-L-proline(in) + L-alanine(out) + Na(+)(in)
  3. D-threonine(out) + L-alanine(in) = D-threonine(in) + L-alanine(out)

  Catalysed by PRODH2, SLC1A4, SLC7A10inner side of the membrane, outer side of the membraneOne of 2 routes

• L-methionineReach from here →
  1. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)
  2. trans-4-hydroxy-L-proline(out) + L-alanine(in) + Na(+)(out) = trans-4-hydroxy-L-proline(in) + L-alanine(out) + Na(+)(in)
  3. transport of alanine and methionine (cytosol to extracellular)

  Catalysed by PRODH2, SLC1A4, SLC7A5inner side of the membrane, outer side of the membrane, extracellular space, cytosolOne of 7 routes

• L-tryptophanReach from here →
  1. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)
  2. trans-4-hydroxy-L-proline(out) + L-alanine(in) + Na(+)(out) = trans-4-hydroxy-L-proline(in) + L-alanine(out) + Na(+)(in)
  3. transport of alanine and tryptophan (cytosol to extracellular)

  Catalysed by PRODH2, SLC1A4, SLC7A5inner side of the membrane, outer side of the membrane, extracellular space, cytosolOne of 4 routes

• glutathioneReach from here →
  1. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)
  2. a quinone + hydrogen sulfide + glutathione + H(+) = S-sulfanylglutathione + a quinol
  3. S-sulfanylglutathione + O2 + H2O = sulfite + glutathione + 2 H(+)

  Catalysed by PRODH2, SQOR, ETHE1One of 2 routes

• L-kynurenineReach from here →
  1. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)
  2. trans-4-hydroxy-L-proline(out) + L-alanine(in) + Na(+)(out) = trans-4-hydroxy-L-proline(in) + L-alanine(out) + Na(+)(in)
  3. L-kynurenine + H2O = anthranilate + L-alanine + H(+)

  Catalysed by PRODH2, SLC1A4, KYNUinner side of the membrane, outer side of the membrane

• beta-alanineReach from here →
  1. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)
  2. trans-4-hydroxy-L-proline(out) + L-alanine(in) + Na(+)(out) = trans-4-hydroxy-L-proline(in) + L-alanine(out) + Na(+)(in)
  3. beta-alanine(out) + L-alanine(in) = beta-alanine(in) + L-alanine(out)

  Catalysed by PRODH2, SLC1A4, SLC7A10inner side of the membrane, outer side of the membraneOne of 2 routes

• L-asparagineReach from here →
  1. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)
  2. trans-4-hydroxy-L-proline(out) + L-alanine(in) + Na(+)(out) = trans-4-hydroxy-L-proline(in) + L-alanine(out) + Na(+)(in)
  3. transport of alanine and asparagine (cytosol to extracellular)

  Catalysed by PRODH2, SLC1A4, SLC7A5inner side of the membrane, outer side of the membrane, extracellular space, cytosolOne of 6 routes

• L-phenylalanineReach from here →
  1. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)
  2. trans-4-hydroxy-L-proline(out) + L-alanine(in) + Na(+)(out) = trans-4-hydroxy-L-proline(in) + L-alanine(out) + Na(+)(in)
  3. transport of alanine and phenylalanine (cytosol to extracellular)

  Catalysed by PRODH2, SLC1A4, SLC7A5inner side of the membrane, outer side of the membrane, extracellular space, cytosolOne of 6 routes

• 3-hydroxy-L-kynurenineReach from here →
  1. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)
  2. trans-4-hydroxy-L-proline(out) + L-alanine(in) + Na(+)(out) = trans-4-hydroxy-L-proline(in) + L-alanine(out) + Na(+)(in)
  3. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)

  Catalysed by PRODH2, SLC1A4, KYNUinner side of the membrane, outer side of the membrane

• 1-hexadecanoylglycerone 3-phosphateReach from here →
  1. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)
  2. a quinone + sn-glycerol 3-phosphate = dihydroxyacetone phosphate + a quinol
  3. dihydroxyacetone phosphate + hexadecanoyl-CoA = 1-hexadecanoylglycerone 3-phosphate + CoA

  Catalysed by PRODH2, GPD2, GNPAT

• N(omega),N(omega)-dimethyl-L-arginineReach from here →
  1. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)
  2. trans-4-hydroxy-L-proline(out) + L-alanine(in) + Na(+)(out) = trans-4-hydroxy-L-proline(in) + L-alanine(out) + Na(+)(in)
  3. N(omega),N(omega)-dimethyl-L-arginine + pyruvate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + L-alanine

  Catalysed by PRODH2, SLC1A4, AGXT2inner side of the membrane, outer side of the membrane

• (2S)-2-[5-amino-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamido]succinateReach from here →
  1. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)
  2. a quinone + succinate = fumarate + a quinol
  3. 1-(5'-Phosphoribosyl)-5-amino-4-(N-succinocarboxamide)-imidazole AMP-lyase

  Catalysed by PRODH2, SDHB, ADSLcytosolOne of 2 routes

• D-glyceraldehyde 3-phosphateReach from here →
  1. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)
  2. a quinone + sn-glycerol 3-phosphate = dihydroxyacetone phosphate + a quinol
  3. D-glyceraldehyde 3-phosphate = dihydroxyacetone phosphate

  Catalysed by PRODH2, GPD2, TPI1

• L-prolineReach from here →
  1. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)
  2. a quinol + 2 Fe(III)-[cytochrome c](out) = a quinone + 2 Fe(II)-[cytochrome c](out) + 2 H(+)(out)
  3. L-proline + a quinone = (S)-1-pyrroline-5-carboxylate + a quinol + H(+)

  Catalysed by PRODH2, CYC1, UQCRFS1, PRODHouter side of the membraneOne of 6 routes

• L-cysteinylglycineReach from here →
  1. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)
  2. trans-4-hydroxy-L-proline(out) + L-alanine(in) + Na(+)(out) = trans-4-hydroxy-L-proline(in) + L-alanine(out) + Na(+)(in)
  3. gamma-glutamyltransferase (alanine)

  Catalysed by PRODH2, SLC1A4, GGTLC3, GGT1 and 4 moreinner side of the membrane, outer side of the membrane, cytosolOne of 2 routes

• Mo-molybdopterinReach from here →
  1. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)
  2. trans-4-hydroxy-L-proline(out) + L-alanine(in) + Na(+)(out) = trans-4-hydroxy-L-proline(in) + L-alanine(out) + Na(+)(in)
  3. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O

  Catalysed by PRODH2, SLC1A4, MOCOSinner side of the membrane, outer side of the membrane

• L-threonylcarbamoyladenylateReach from here →
  1. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)
  2. trans-4-hydroxy-L-proline(out) + L-threonine(in) + Na(+)(out) = trans-4-hydroxy-L-proline(in) + L-threonine(out) + Na(+)(in)
  3. L-threonine + hydrogencarbonate + ATP = L-threonylcarbamoyladenylate + diphosphate + H2O

  Catalysed by PRODH2, SLC1A4, YRDCinner side of the membrane, outer side of the membrane

• (2S)-2-aminobutanoateReach from here →
  1. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)
  2. trans-4-hydroxy-L-proline(out) + L-alanine(in) + Na(+)(out) = trans-4-hydroxy-L-proline(in) + L-alanine(out) + Na(+)(in)
  3. 2-oxobutanoate + L-alanine = (2S)-2-aminobutanoate + pyruvate

  Catalysed by PRODH2, SLC1A4, AGXT2inner side of the membrane, outer side of the membrane